Patent GB-524996-A (GB)
Title: Treatment of maleic anhydride-styrene resin or like resin
IPC: C08F8/30
Filed: 1939-01-16
Abstract: 524,996. Photographic materials. KODAK, Ltd. (Eastman Kodak Co.). Jan. 16, 1939, Nos. 1430 and 29661. [Class 98 (ii)] [Also in Group IV] Resinous condensation or polymerization products containing amino groups attached to a benzenoid nucleus are prepared by reduction of the product obtained by nitrating a resinous product containing a benzenoid nucleus. The amino-resins may be diazotized and resinous dyes are prepared by coupling the diazotized resin. Suitable resinous products to be treated include interpolymers of styrene and maleic anhydride, methyl acrylate, methyl methacrylate or acrylic acid, polystyrene, polydi- ' hydronaphthalene, interpolymers of dihydronaphthalene and maleic anhydride, coumaroneindene resins, reaction products of polyacrylyl chloride and aniline and soluble phenol-formaldehyde resins ; suitable coupling components include aromatic diamines such as o- or p-phenylene diamine, alkylated aromatic amines such as o-toluidine, sulphonated aromatic amines such as amino G salt, H acid, naphthionic acid, nitrated aromatic amines such as pnitraniline, phenols and naphthols, sulphonated phenols and naphthols such as 2:6:8-naphtholdisulphonic acid, naphthoic acids such as hydroxynaphthoic acid, and diphenylamine. The nitro resins to be reduced are prepared by treatment with fuming nitric acid, the resin, if desired being in solution in nitrobenzene ; reduction may be effected electrolytically, by metal such as tin or iron in acid medium or by reducing agent such as alkaline sodium hydrosulphite. Diazotization may be effected by the use of acid and a nitrate or by means of oxides of nitrogen in the presence of water ; coupling is effected as in the normal production of azo-dyestuffs. Dyes specified include " amino " styrene-maleic anhydride resin # #-naphthol (alkaline salt red, free acid bluish red), " amino" styrene-maleic anhydride resin # resorcinol (brick red), " amino " styrene-maleic anhydride # toluidine (orange), " amino " polydihydronaphthalene # #-naphthol (wine-red), " amino " styrene-methyl methacrylate resin # #-naphthol (orange-red), " amino " dihydronaphthalene-maleic anhydride resin # #-naphthol (deep-red), " amino " styrene-' resin # #-naphthol (bright red), " amino " styrene-acrylic acid resin # #-naphthol (bright red). The resin dyes may be used as non- diffusing colours in photographic antihalation layers ; they may be coated on to a film and removed during alkaline development since they are alkali-soluble ; the diazotized resin may be added to photographic emulsions, cloth or thread and the resin coupled ; the resin dyes may also be used as pigments. The amino-resins may be used as dispersing agents for water-insoluble material such as micro-crystals of silver halide to prevent lom eration. Light sensitive silver halide emulsions may be prepared using the aminoresin as the dispersing agent and gelatine or the resin as the carrier. The amino-resins may also be used in photographic film as an emulsion support or as antistatic, antihalation or abrasion resistant layers or as interlayers between the emulsion and the support.